$39 Cheap Flights from Louisville (SDF) to Chicago (MDW)

View $39 flight on Wed, Jun 18, 2025Opens in a new window

Popular airlines from Louisville Intl. Airport (SDF) to Chicago Midway Airport (MDW)

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Find available prices by choosing your travel dates.

Cheap Flights from Louisville to Chicago (SDF-MDW)

Prices were available within the past 7 days and start at $39 for one-way flights and $77 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Jul 3 - Mon, Jul 7
SDF
Louisville
MDW
Chicago
$77 Roundtrip, found 3 hours ago
$77
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Jul 3 from Louisville to Chicago, returning Mon, Jul 7, priced at $77 found 3 hours ago
Southwest Airlines
Wed, Aug 20 - Thu, Aug 28
SDF
Louisville
MDW
Chicago
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Louisville to Chicago, returning Thu, Aug 28, priced at $97 found 2 days ago
Southwest Airlines
Wed, May 21 - Thu, May 22
SDF
Louisville
MDW
Chicago
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, May 21 from Louisville to Chicago, returning Thu, May 22, priced at $97 found 3 days ago
Southwest Airlines
Thu, Jul 3 - Mon, Jul 7
SDF
Louisville
MDW
Chicago
$107 Roundtrip, found 3 hours ago
$107
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Jul 3 from Louisville to Chicago, returning Mon, Jul 7, priced at $107 found 3 hours ago
Southwest Airlines
Thu, Jun 5 - Thu, Jun 12
SDF
Louisville
MDW
Chicago
$112 Roundtrip, found 3 days ago
$112
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Jun 5 from Louisville to Chicago, returning Thu, Jun 12, priced at $112 found 3 days ago
Southwest Airlines
Mon, Jun 9 - Tue, Jun 10
SDF
Louisville
MDW
Chicago
$114 Roundtrip, found 7 hours ago
$114
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Mon, Jun 9 from Louisville to Chicago, returning Tue, Jun 10, priced at $114 found 7 hours ago
Southwest Airlines
Sat, Jun 7 - Tue, Jun 10
SDF
Louisville
MDW
Chicago
$124 Roundtrip, found 8 hours ago
$124
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Sat, Jun 7 from Louisville to Chicago, returning Tue, Jun 10, priced at $124 found 8 hours ago
Southwest Airlines
Fri, May 23 - Mon, May 26
SDF
Louisville
MDW
Chicago
$125 Roundtrip, found 1 hour ago
$125
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Fri, May 23 from Louisville to Chicago, returning Mon, May 26, priced at $125 found 1 hour ago
Southwest Airlines
Wed, Aug 20 - Thu, Aug 28
SDF
Louisville
MDW
Chicago
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Louisville to Chicago, returning Thu, Aug 28, priced at $127 found 2 days ago
Delta
Tue, Jun 10 - Thu, Jun 12
SDF
Louisville
MDW
Chicago
$127 Roundtrip, found 7 hours ago
$127
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Jun 10 from Louisville to Chicago, returning Thu, Jun 12, priced at $127 found 7 hours ago
Flights from Louisville (SDF) to Chicago (MDW)
Origin airport
Louisville Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$71
Distance
270 mi

Louisville to Chicago Flights

The cheapest times to fly from Louisville to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Louisville to Chicago are during the month of July. You can find some of the cheapest flights from Louisville to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Louisville to Chicago

Sunday is one of the best days to book for cheap flights from Louisville to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Louisville to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Louisville to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $39 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Louisville to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Louisville to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW) cost?
Cheap return flights from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW) start from $97. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving SDF on May 21 2025 and touching down at MDW. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from SDF to MDW?
The cheapest flights from SDF to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW)?
Fly directly from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from SDF to MDW?
With prices starting from $49 for a one-way flight from SDF to MDW, Southwest Airlines is currently the cheapest airline on this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SDF on June 5 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW)?
When jetting out of Louisville Intl. Airport (SDF), you’ll have your pick from an average of 2 daily direct flights to Midway Intl. Airport (MDW).
What are the most popular departure times for flights from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW)?
Flights between SDF and MDW tend to be busiest at 7 AM. For a quieter experience and potentially cheaper prices, look for a time outside the usual busy windows.
What day of the week has the most flights from SDF to MDW?
Friday offers the most flights from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW). Consider taking off on this day and you’ll have a greater chance of finding a departure that fits your itinerary.
What is the earliest flight from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW)?
Take the earliest flight at around 7:05AM UTC-5, heading out of Louisville Intl. Airport (SDF). You’ll be traveling for around 1h 15m, landing at Midway Intl. Airport (MDW) at approximately 7:20AM UTC-6.
How long does it take to fly from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW)?
It takes approximately 1 hour and 18 minutes to cover the 270 mi from SDF to MDW.
What airline has the least delays from SDF to MDW?
Southwest Airlines has the best performance for on-time direct flights from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW), with an on-time score of 89%. Use the Expedia App to check your flight schedule before you take off and get real-time alerts about any changes.
What is the best time to fly from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) without delays, pick a flight that takes off from Louisville Intl. Airport (SDF) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Louisville Intl. Airport (SDF)?
You can arrive at O’Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when traveling to Chicago on a direct flight from Louisville Intl. Airport (SDF).
Is it cheaper to buy a plane ticket from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from SDF to MDW are usually more expensive. To secure the best rates, start looking for flights early. That said, if your travel plans are flexible, you may score a cheap fare right before you leave.
Is it cheaper to book a SDF to MDW flight and hotel package?
You can save money by securing a SDF to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s easy to manage it all in one convenient place. After selecting your preferred accommodations and flights, you can add extras such as car rentals, activities and tours.
Can I cancel or change the date of my flight from Louisville Intl. Airport (SDF) to Midway Intl. Airport (MDW)?
Typically, you can cancel or reschedule your SDF to MDW flight. However, additional fees may apply, especially if your booking was made more than 24 hours ago. Double-check your itinerary for the airline’s fees and rules on flight changes, or if you want further details, visit our Customer Service portal.

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